3-Methyl-1,2-cyclopentanedione → 5-(6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylimino)-2-methylcyclopent-1-enol

HRID 572901

반응식

HRID 572901 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:25][CH:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1)[C:11]1[CH:12]=[C:13]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH:14]=[CH:15][C:16]=1[F:17].C([O-])(=O)C([O-])=O.[CH3:39][CH:40]1[CH2:44][CH2:43][C:42](=O)[C:41]1=[O:46]>C(O)C.O.[OH-].[Na+]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:25][CH:26]1[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]1)[C:11]1[CH:12]=[C:13]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]=[C:42]2[C:41]([OH:46])=[C:40]([CH3:39])[CH2:44][CH2:43]2)[CH:14]=[CH:15][C:16]=1[F:17]

참가 물질

7

반응물 3

HCID 612093-Methyl-1,2-cyclopentanedioneHCID 71081OxalateHCID 668361616-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylamine

생성물 1

HCID 668358735-(6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylimino)-2-methylcyclopent-1-enol

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

A mixture of 6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylamine, oxalate (example 557, 50 mg), 3-methyl-1,2-cyclopentanedione (11.8 mg) in ethanol (2 mL) is refluxed for 2 h. The mixture is then cooled, diluted with water and 1N sodium hydroxide and extracted with ethyl acetate. Pooled extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0.5 to 95/5/0.5) to afford 5-(6-{3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]-4-fluorophenyl}hex-5-ynylimino)-2-methylcyclopent-1-enol. TLC (Eluent: CH2Cl2/MeOH/NH4OH 95/5/0.5) Rf=0.30.

후처리

  1. temperatureis refluxed for 2 h
  2. temperatureThe mixture is then cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialPooled extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0.5 to 95/5/0.5)

출처 및 근거

ORD 기록
ord-34c2fae662ec423da2c304810998ff4d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029357B2

연결된 노트

불러오는 중…